The azole group of antifungal agents constitutes an important class of compounds useful in the treatment of various fungal infections. Fluconazole is one of the most important members of the family of azole antifungals as it is orally active and has low toxicity, but its extensive use has resulted in emergence of fluconazole-resistant fungal strains. This has made it necessary to develop analogues of fluconazole effective against resistant strains, and many new compounds have been reported. However, the issues like toxicity, solubility, cost, broad spectrum of activity, etc, make it inevitable to develop superior antifungal agents. The structure-activity relationship studies in case of fluconazole have shown that presence of one triazole ring, halogenated phenyl ring and tertiary alcoholic oxygen functionality is necessary for activity.
Some of the recent references describing synthesis and antifungal activity of fluconazole analogues are described in the following articles:
Chemistry and Biodiversity 4, 1472 (2007); Bioorg. Med. Chem. Lett. 17(13), 3686 (2007); Bioorg. Med. Chem. 16, 7055 (2008); Bioorg. Med. Chem. Lett. 18, 3261 (2008); Bioorg. Med. Chem. Lett. 18, 6538 (2008); Bioorg. Med. Chem. Lett. 19, 2013 (2009); and Bioorg. Med. Chem. Lett. 20, 722 (2010).
The compounds described in the present invention are however new compounds, and there is no prior art available for preparation of these compounds. Thus, the present invention seeks to provide novel azoles containing pharmacophores and their preparation as an effort to come up with antifungal agents with superior antifungal activity.